Resequinil, AVE-3933, SX-3933, AC-3933
雷地奎尼Chemical Name: 5-(3-Methoxyphenyl)-3-(5-methyl-1,2,4-oxadiazol-3-yl)-1,6-naphthyridin-2(1H)-one
CAS No. 219846-31-8
项目整合开发状态: Phase II
项目研究机构: Dainippon Pharmaceutical (Originator), Aventis Pharma (Licensee)
合成路线:The reaction of 3-methoxybenzoylacetone (I) with dimethylformamide dimethylacetal (II) gives the dimethylaminomethylene derivative (III),which is cyclized with 2-cyanoacetamide (IV) by means of sodium ethoxide in ethanol yielding the pyridinone (V).The condensation of (V) with dimethylformamide dimethylacetal (II) affords the dimethylaminovinylpyridinone (VI),which is cyclized by means of ammonium acetate in DMF providing the 1,6-naphthyridine (VII).The hydrolysis of the cyano group of (VII) with NaOH gives the corresponding carboxylic acid (VIII),which is finally cyclized with N-hydroxyacetamidine (IX) by means of carbonydimidazole (CDI).
📌 参考资料/链接：
参考文献标题:Structure-activity relationships and cognition-enhancing actions of novel 1,6-naphthyridine derivatives with benzodiazepine receptor inverse agonists activities
文献作者:Masumoto,K.; et al.
参考来源:Symp Med Chem 1998,Abst 2-P-10
📄 详细内容
合成路线:The reaction of 3-methoxybenzoylacetone (I) with dimethylformamide dimethylacetal (II) gives the dimethylaminomethylene derivative (III),which is cyclized with 2-cyanoacetamide (IV) by means of sodium ethoxide in ethanol yielding the pyridinone (V).The condensation of (V) with dimethylformamide dimethylacetal (II) affords the dimethylaminovinylpyridinone (VI),which is cyclized by means of ammonium acetate in DMF providing the 1,6-naphthyridine (VII).The hydrolysis of the cyano group of (VII) with NaOH gives the corresponding carboxylic acid (VIII),which is finally cyclized with N-hydroxyacetamidine (IX) by means of carbonydimidazole (CDI).
参考文献标题:Synthesis and pharmacological evaluation of novel 3-oxadiazolyl-1,6-naphthyridines as a new class of potential cognitive enhancers
文献作者:Odai,O.; et al.
参考来源:15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998,Edinburgh) 1998,Abst P.256
产品链接: CAS No. 219846-31-8››